It looks like Jon Gruden has caught a little bit of the March Madness fever—courtesy of Kentucky Basketball. The former Super Bowl-winning coach and current Barstool Sports media personality recently received a special care package from the Wildcats to enjoy the tournament in style.
Gruden, who rose to NFL fame with successful coaching stints with the Oakland Raiders and Tampa Bay Buccaneers, has always been a charismatic figure in the sports world. As the youngest head coach to win a Super Bowl at age 39, Gruden led the Buccaneers to their first-ever title in 2002. After his time on the sidelines, he spent nearly a decade as an analyst for ESPN’s Monday Night Football, cementing his reputation as one of the most knowledgeable voices in the game.
In 2023, Gruden was brought in by the New Orleans Saints to help out with their offensive coaching during a workout, proving that even years removed from the main stage, his football mind remains sharp. Now, in 2025, he’s taken on a new chapter with Barstool Sports, where he continues to deliver his trademark blend of insight and entertainment.
But it appears Gruden’s interest in sports isn’t limited to just football. With March Madness in full swing, Kentucky Basketball made sure the former coach had all the essentials to fully immerse himself in the tournament atmosphere. The Wildcats sent Gruden a customized care package filled with Kentucky-themed swag meant to enhance his viewing experience.
Our first BASKETBALL box comes courtesy of Coach Pope and @KentuckyMBB! So much tradition and history, what an awesome gift to receive!
— Jon Gruden (@BarstoolGruden) March 13, 2025
Just in time for the Tournament, too! pic.twitter.com/C88XPFsLBc
Social media buzzed when Gruden shared a photo of the package on his Barstool Sports profile, expressing his gratitude to the Wildcats and playfully mentioning that Kentucky’s hospitality just might make him root for the Big Blue during the tournament. Fans immediately responded, sharing their excitement and encouraging Gruden to join Big Blue Nation for the ride.
It’s no secret that Kentucky’s fanbase is one of the most passionate in college basketball. And whether Gruden ends up donning Kentucky blue for the duration of March Madness or not, it’s clear that the Wildcats made a lasting impression on the former NFL head coach.
With Selection Sunday today, Kentucky Basketball’s gesture of goodwill adds yet another layer of excitement to the most thrilling time of the year for hoops fans. And who knows? Maybe Jon Gruden’s new fandom will bring a little extra luck to the Wildcats this postseason.